Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols

Organic Letters

Volumn 1, Issue 3, 1999, Pages 447-450

  Martinelli, Michael J ^a   Nayyar, Naresh K ^a   Moher, Eric D ^a   Dhokte, Ulhas P ^a   Pawlak, Joseph M ^a   Vaidyanathan, Rajappa ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000941585     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990658l     Document Type: Article

References (29)

1. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
2. O'Donnell, C. J.; Burke, S. D. J. Org. Chem. 1998, 63, 8614.
3. Bouzide, A.; Sauvé, G. Tetrahedron Lett. 1997, 38, 5945.
4. Sekine, M.; Kume, A.; Hata, T. 3617; Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1993, 58, 3791.
5. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1810.
6. Shanzer, A. Tetrahedron Lett. 1980, 21, 221.
7. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
8. Boons, G.-J.; Castle, G. H.; Clase, J. A.; Grice, P.; Ley, S. V.; Pinel, C. Synlett 1993, 913.
9. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373.
10. Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
11. Steliou, K.; Nowosielska, A. S.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7579.
12. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
13. Whitesell, J. K.; Apodaca, R. Tetrahedron Lett. 1996, 37, 2525.
14. (a) Morcuende, A.; Valverde, S.; Herradón, B. Synlett 1994, 89.
15. (b) Herradón, B.; Morcuende, A.; Valverde, S. Synlett 1995, 455.
16. Morcuende, A.; Ors, M.; Valverde, S.; Herradón, B. J. Org. Chem. 1996, 61, 5264.
17. Maki, T.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 1998, 39, 5601.
18. Wittenberger, S. J.; Donner, B. G. J. Org. Chem. 1993, 58, 4139.
19. Trimurtulu, G.; Ohtani, I.; Patterson, G. M.; Moore, R. E.; Corbett, T. H.; Valeriote, F. A.; Demchik, L. J. Am. Chem. Soc. 1994, 116, 4729.
20. 13C NMR, IR, HRMS, EA) and were compared to literature values or commercial samples whenever possible.
21. 1H NMR.
22. (a) Wrackmeyer, B. Ann. Rep. NMR Spectrosc. 1985, 16, 73.
23. (b) Roelens, S.; Taddei, M. J. Chem. Soc., Perkin Trans. 2 1985, 799.
24. (c) Otera, J.; Yano, T.; Okawara, R. Chem. Lett. 1985, 901.
25. (d) Otera, J.; Yano, T.; Okawara, R. Organometallics 1986, 5, 1167.
26. Luchinat, C.; Roelens, S. J. Org. Chem. 1987, 52, 4449.
27. (a) Shanzer, A.; Libman, J.; Gottlieb, H. E. J. Org. Chem. 1983, 48, 4112.
28. (b) Luchinat, C.; Roelens, S. J. Am. Chem. Soc. 1986, 108, 4873.
29. Roelens, S. J. Org. Chem. 1996, 61, 5257.